Reacción #1100489

Ecuación de reacción

HCl

mixture

methyl 3-bromo-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1H-indole-2-carboxylate

NaOH

methanol

→

title compound

3-bromo-4-(2-methylphenyl)-1-(3-(1-naphthyloxy)propyl)-1H-indole-2-carboxylic acid

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated
2. 2
   OtroThe residue was purified by RPHPLC (mobile phase: 10%-100% acetonitrile in 0.1% TFA aqueous solution during 60 minutes) on a C18 column

Procedimiento

A mixture of EXAMPLE 126C (22 mg), NaOH (0.167 ml), methanol (1.5 ml) and tetrahydrofuran (1.500 ml) was stirred at room temperature for 36 hours, acidified with HCl and concentrated. The residue was purified by RPHPLC (mobile phase: 10%-100% acetonitrile in 0.1% TFA aqueous solution during 60 minutes) on a C18 column to provide the title compound. 1H NMR (500 MHz, dichloromethane-d2) δ 8.30-8.40 (m, 1H), 7.79-7.85 (m, 1H), 7.56 (d, J=8.54 Hz, 1H), 7.47-7.55 (m, 2H), 7.43 (d, J=8.24 Hz, 1H), 7.35 (t, J=7.93 Hz, 1H), 7.28-7.33 (m, 2H), 7.20-7.27 (m, 2H), 7.13-7.18 (m, 1H), 6.93 (d, J=7.02 Hz, 1H), 6.75 (d, J=7.63 Hz, 1H), 4.78-5.03 (m, 2H), 4.16 (t, J=5.65 Hz, 2H), 2.37-2.54 (m, 2H), 2.01 (s, 3H).

Fuente